I think gwen Stacy is #1, mainly because of when it happened. As I told Gerry Conway at a comic-con a few years ago "Nowadays, death of anyone in comics now loses its' sting. They killed Superman fer crying out loud, no one is safe." But in 1973, this was brand new territory. Gwen Stacy wasn't evne that major of a character, and it was still a shock.
One that I'd put on if I made a list would be Superboy in LSH #38. Byrne kinda messed with the Legion when he decided to get rid of the Superboy mythos as we knew it. SO, this changed a lot of things, not just the history of the LSH, and Superman's past. It took the Time Trapper from pesky, pretty powerful villain, to a cosmic entity, capable of creating his own universes. In the end, this Superboy dies to save a reality that isn't even his own. Pretty darn self-less.
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